


The Mad Hatter

by Caramell0w



Category: Jefferson - Fandom, Mad Hatter - Fandom, Once Upon A Time - Fandom
Genre: Alternate Universe - College/University, Angst with a Happy Ending, F/M, Fluff, Happy Ending, Light Angst, Reader-Insert, Smut in chapter 4
Language: English
Status: Completed
Published: 2018-12-04
Updated: 2018-12-04
Packaged: 2019-09-07 04:21:42
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 9,571
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16847032
Author URL: https://archiveofourown.org/users/Caramell0w/pseuds/Caramell0w
Summary: Jefferson dates for money; but you're the girl he wants to change for





	1. Chapter 1

**Author's Note:**

> This was written for the lovely @learisa on Tumblr.

**Jefferson:**

The money is good and the girls are hot; so why am I suddenly having a problem with my job? One name jumps to mind— Y/N. She’s the reason I’m contemplating giving up this lucrative business arrangement. I don’t want to date and run anymore. I want to be able to spend time with her because  _ I _ want to; not because I’m getting paid to. If she ever finds out, I’m so screwed.

Let’s back up a bit, and revisit how I got into this situation in the first place. My name is, Jefferson Hatter. A few years ago as a joke, I came up with the idea of starting a dating business to help pay for college expenses. I’m hired by others to take unsuspecting girls on a date or two. It’s strictly business, and I never get too involved. The reasons why the dates are needed are inconsequential. As long as the money is good, their reasons are for them alone.

I’m known around campus as a serial dater, never getting too serious. However, my clients call me,  _ The Mad Hatter _ . It’s a play on my last name, and it’s not because I’m mad— because people think I’m crazy. Crazy or not, most clients tell me it was the best investment and they’re happy with services provided. 

Of course, just like any business deal, there are some clauses to my ventures. I don’t do more than three dates with the same girl. It’s not fair to her, and I don’t want her to begin developing feelings for me. I won’t do more than a good night kiss (and no, you can’t pay me for more, I have  _ some _ standards). If we are going somewhere that will cost me more than $40, the client is responsible for the difference. 

Other than that, I don’t care, and I’ll go on a date with any female— short, tall, round, thin, dark or light skinned, it doesn’t matter to me. A job is a job in the end; and let me tell you, my business has really taken off. I tried hiring a friend to help with the amount of dates; but after one date with a girl that ended badly; I had to dump him. I don’t trust anyone else to not fuck things up on me. You know the saying: If you want something done right, you have to do it yourself. 

Clients find me through work of mouth. I don’t advertise; but I check out the wanted adds on the school website. That’s where this story really begins.

**Wanted:**

_ Looking for a date for my girlfriend’s roommate. Call Chad at 555-555-0185 for information. _

“Perfect,” I mumble, pulling out my phone to dial Chad’s number. 

“Hello?” He answers on the third ring.

“Hi, I saw your help wanted ad on the school website about needing a date for your girlfriend’s roommate?

“Oh shit, are you the guy?” He sounds a little to excited.

“I’m answering an ad, if that’s what you mean.”

“No, the one that does this all the time. Are you him? My buddy Frank, said to put the ad up and you’d call.”

_ Frank.  _ He’s my buddy that couldn’t keep it in his pants and I had to drop him. He doesn’t talk to me too often anymore; but he is still good for recommending clientele. 

“Yes. I’m him.”

“Great, not sure how this works, or anything; but I’m desperate.”

“Well there’s a contract we both need to sign and we need to discuss the terms of the agreement. How about you meet me at Granny’s in an hour? You can buy me a coffee.”

“Great. What’s your name so I can ask for you?”

“Just call me,  _ The Mad Hatter.” _

* * *

**Y/N**

“Aubrey, I have a lot of work I need to finish here. Can’t you find someone else to go with Chad’s friend tonight?”

“No, I told Chad I want to double with you, and he said he’s find the guy. It’s final. I need you to get your ass off this bed, close your computer, and get ready. Your homework can wait until tomorrow. Besides, it’s good to get out and date. You’re never going to find someone with your nose always stuck in a book.”

Ah! The same thing she tells me almost every weekend, when I tell her I have no plans. The thing is, I like having my nose in a book. It’s hard to keep my grades top notch if I have distractions, so I just removed them from my life. It’s easier this way.

I open my mouth to speak and she shuts me down. 

“Don’t you dare tell me about your grades or your future plans again. I don’t care. I don’t want to know. I want you to come on a double date with me, so we can all have a good time.”

“Aubrey, how would going on a blind date, with someone who probably isn’t even my type, going to help. No offence to Chad; but I assume most of his friends are like him, and we have nothing in common. He’s a jock and I’m a bookworm. I don’t even like going to the games you drag me to.”

“He promised me it would be someone other than one of his friends. Come on, it will be fun!” She sits down on the bed next to me. “I miss hanging out with you. You are all work and no play anymore. Remember when we first met? We promised we would hang out all the time, and now all I see is the top of your head. If you do this for me. I’ll leave you alone for a month. I won’t push you into anything else; but you have to actually  _ try _ to have fun tonight.”

I turn to face her and roll my eyes. “Fine. I’ll try. I make no promises though. We probably won’t even get along.”

“That’s not trying. You need to have a positive attitude.” She smiles wide and I return the gesture. “Perfect. Now, let’s get you ready for this date.” 

She grabs my arm and pulls me over to my small closet. She digs through, and settles on a dark purple dress that sits just above my knee and a pair of wedge sandals. I give her a look, letting her know I’m not sure about her choice, and she scowls. I take the dress from her outstretched hand and head to the bathroom to change. 

I put it on, apply a subtle amount of makeup to make my eyes pop, and pull my hair away from my face. I walk back into our room and Aubrey looks like a model— as usual. I swear, that girl could make a plastic bag stylish.

“When are they going to be here?”

“Now.” Chad answers behind me. I turn to look at him, and the other man who has walked in with him.  _ Holy hell in a handbasket! _ Jefferson is with him. I have been lusting after this man since we were in the same World History class sophomore year. His dark hair and striking blue eyes make all the girls swoon; and I’m sure he’s rocking a great body under his black shirt and dark wash jeans.

“Ladies, let me introduce you to my friend, Jefferson. Jefferson, this is my girlfriend, Aubrey, and her roommate, Y/N.”

“Nice to meet you, Aubrey.” He turns and directs his attention on me. “Y/N, you look lovely in that dress.” 

The compliment is nice, and coming from him makes me ecstatic; but I can’t shake the feeling something isn’t...genuine. 

“How do you two know each other?” I ask, looking between Chad and Jefferson.

“We have a mutual friend. Shall we get going? Don’t want to be late for the party.” Chad replies. He grabs Aubrey’s hand and all but drags her out of the dorm room. She giggles and wraps her other arm around his.

“Ladies first,” he motions for me to exit, and I do with a small huff of annoyance.  _ Something’s going on here, and I’m going to find out what it is. _

* * *

 

**Jefferson**

Y/N. My date for the night is Y/N. I’ve seen her around campus, her nose always in a book. We had a class together and I used to sit behind her, admiring how shiny her hair looked. This girl is a lot smarter than the others I’ve gone on dates with. She’s not going to be an easy sell. I clear my throat and she beats me to the punch.

“Listen, Jefferson, I’m not sure what’s in this for you; but I’m just doing this as a favor to my friend. I’m supposed to actually  _ try  _ to have a good time tonight. So, do me a favor and is Aubrey asks, tell her we are having a great time.”

I laugh. She has no idea what’s in it for me; but the words make me nervous she’s figured it out already. “Y/N, how about we actually try to have some fun then. Listen, I know you’re the girl who would rather lie on the grass reading a book, than go to some frat party. I also know you are one of the smartest girls in at the University. I just want to take the evening to get to know you and if there is something there, then we can explore it.”  _ Or if Chad decides he needs to buy my time again. _

“Fine. What are you studying?” 

She tries to walk a few steps in front of me; but I catch up easily. My height and long legs make it simple to do so. 

“I’m a psychology major, how about you?”

“Business and history, double major.”

“Now I understand why you’re always studying.” I smile, trying to reassure her and she crosses her arms. She’s closing herself off to me. 

“Yes. Does it bother you? I have a full caseload this semester, and I’m trying to maintain my GPA.”

_ Time to lay on the charm.  _ “No, I like a girl who’s smart. Maybe I can join you on the quad sometime and we can study together.”

A line forms between her brows. “We aren’t in any of the same classes. How do you expect to study together?”

“Well I figure we could just keep each other company. Sometimes it makes it easier knowing someone is working towards a similar goal.” It’s a crap lie, but it’s the best I can come up with on the fly.

She shrugs and picks up her walking pace again. “Never heard that before.” 

“Slow down, will ya? Are you that desperate to get to the dull party? We are probably going to be bored to tears.” I catch up with her easily again.

The remark earns me a smile from her. “No, I actually could care less about going to this stupid party. I’m going because Aubrey wants me to. She thought it would be fun doing a double date; but I thought dinner or something, not a frat party. How the hell is anyone supposed to talk when everyone is too busy getting drunk or trying to get laid?”

“I’d be happy to get something to eat with you instead. We can head to Granny’s and get a bite and get to know one another?”

“Really?”

I smile and nod. “Yeah. It sounds like a better use of my time.”

She hugs herself and nods. “Yeah, I’d like that alot.”

“Come on, my car is just down there,” he points to the parking lot on the lower part of campus. “I’ll drive us over.”

Our conversation flows easily as we make our way to Granny’s. She’s discussing the parallels of history and business and why they are such a great set of subjects to study. I’m listening to her, and giving the appropriate nods and small hums of acknowledgement; but I’m not entirely listening. This girl is already so different than the others I’ve been out with. She’s passionate, and knows what she wants in life. 

“So, why psychology? What do you hope to do with the degree?”

Her question brings me back into the conversation. “Oh. Well, I find the human psyche interesting. Why do we do the things we do? Why do we feel we have to act a certain way? If someone were you lose something, or someone why do they grieve differently than someone else?” I shrug. “I plan on helping people that are lost, or don’t know what to do.”

My answer must have been surprising to her because she smiles and looks towards her feet. “That’s actually sweet. Knowing you want to help people.”

We take a seat in a booth towards the back of the shop, and order burgers, fries, and a soda. The waitress sets our drinks in front of us, and Y/N plays with the straw, eyes focused on it.

“Tell me more about yourself. I want to know everything,” I smile, encouraging her to share more about herself.

* * *

 

**Y/N**

He’s caring. The way he talks about wanting to help others is so sweet, and my crush is growing larger for this man. Most guys don’t care about anything besides their next lay; but Jefferson...he’s different. A girl walks by our booth on the way to the restroom and she sneers at him. I hear her mutter,  _ pig _ , under her breath.

“What’s that about?”

He shifts in his seat, and offers me a small smile. “Sorry about that, we went on a date a while back and she’s still mad that it didn’t work out.”

“Oh. Well, it’s not like that’s your fault. If it didn’t work, it didn’t work.”

“Yeah. Right.” 

Our food arrives just in time to avoid any awkward lulls in the conversation. Food fills the moments of silence, and we have a great chat in between eating.

“Favorite color?” I ask, dipping my fry in some ketchup.

“Red, and you?”

“Green.”

“Favorite thing to do.”

“I love to watch the stars. I like driving outside the city limits, where there is no light pollution and looking up into the vast sky. There is nothing more beautiful and relaxing that watching the stars twinkle in the night sky. Wanna go sometime? It has to be a clear night.”

I widen my eyes,  _ I just asked him on a date. _ The way he is shifting, he’s uncomfortable. Shit. I’ve ruined this. I need to take it back. “Don’t feel you have to, I just thought you might want to see it. Not like a date, or anything. Just as friends, if you want to. No pressure though.” I’m rambling now. Great, he’s going to think I’m crazy!

He chuckles. “I’d like to see it sometime. My schedule is crazy the next few weeks. Maybe soon though?”

“Yeah, totally. No pressure or anything. Don’t feel like you have to.” I pull my phone from my purse and see several texts and a few missed calls from Aubrey. “Shit. I have to call Aubrey, she’s freaking out because we never showed up at the party. Be right back.”

I scoot out of the booth and step outside into the crisp air. She answers on the first ring. “Where the hell are you? I’ve been worried sick when you didn’t arrive. Chad said not to worry; but I don’t know this guy. For all I know, you could have been kidnapped or lying in a ditch somewhere.”

_ Just like Aubrey to overreact. _ “I’m fine. We both thought the frat party idea was lame and we went to Granny’s for a bite to eat. Do you want us to still come by the party? I’m sure we are getting ready to leave soon.”

“No, it’s fine. I’m heading over to Chad’s for the night, so enjoy the room alone...or maybe not alone, if you know what I mean.” I can hear her smiling through the phone and I roll my eyes at her.

“Bye Aubrey.” 

I turn to head back inside and I almost run down the girl from earlier. “Oh, I’m so sorry. I wasn’t looking where I was going.” I say, trying to steady myself.

“Be careful with him. He’s not what you think, and you’re going to get hurt; just like me.” She walks off, not allowing me to ask anything else.

Jefferson meets me at the door. I’m watching the girl walk away, trying to process what he said. “Yeah. I’m alright. I, um...I’m just a bit tired I guess. Would you mind just taking me home?”

He narrows his eyes at me, trying to figure out my mood change, but offers a single nod. “Sure, come on.”


	2. Chapter 2

**Summary for the Chapter:**

> Jefferson has been hired to take you on a second date. will sparks fly, or will everything come crashing down?

**Y/N**

It’s been two weeks since my date with Jefferson. I try my best not to think of him, or the strange conversation with the girl, but I can’t seem to get either out of my head.  _ Be careful with him.  _ What did she even mean by that? I need to focus on my grades, and the only way I am going to do that is to get the cute boy out of my damn mind. 

I’m staring at my ceiling again, dreaming about what it would be like to feel his lips on mine, or his hands on my body. His voice was like silk, and everytime I think of it, goosebumps erupt on my skin. I take a deep breath in, hold it for a second; then push it out through my nose. I repeat this again and again until the image of his face leaves my mind.

_ I’m not getting any work done here.  _ I stand up, pack a few books in my backpack and decide some fresh air will do me good. I find my favorite spot of the quad, spread out a small blanket, and lay on my stomach, opening my book again. I hear voices around me— kids playing ball, others laughing and carrying on conversations. It’s normal, and it helps clear my mind.

“Always with your nose in a book,” Jefferson chuckles.

My heart rate picks up and I look up at him, squinting to see him from the sun. “Need to keep my grades up. What are you doing here?”

“Hoping to run into you. Mind if I sit down?” He motions towards the empty spot on the blanket next to me.

“Sure.” 

He sits down, and watches as I turn my attention back to my reading. He smells so good, and I can see him out of the corner of my eye. He’s watching me, and smiling. A small army of butterflies erupt in my stomach and I finally give in and look over at him.

“Is there something you want to say?”

“You look really nice today. I like seeing you like this, in your element.”

I laugh, “strange compliment, but I’ll take it. Thanks. You look good yourself.”

I swear a see a small blush on his cheeks and he ducks his head, mumbling his thanks.

“So listen, Y/N, I was hoping we could have that date going out to see the stars?”

My eyes light up, “Yeah, I’d like that a lot. When are you thinking?”  

“I checked the weather and it’s supposed to be a clear night. We could head out there tonight if you’re up for it.”

I nod. I want to say more, but I don’t want to make a fool of myself either. 

“Great, I’ll come by at eight tonight to get you. Is there anything I should bring?” 

“No, just yourself and maybe a sweatshirt. It can get chilly at night.”

“Okay. I’ll see you tonight.” He stands up and saunters off. 

I can’t help the smile that has taken over my face, and I text Aubrey. 

_ Me: Jefferson just asked me out again. We are going to go look at the stars. I shouldn’t be excited...but I am. Need your help tonight to get ready. _

_ Aubrey: That’s awesome! So excited for you. Chad and I have a date night too! We need to try for an actual double soon if this keeps going :) _

I pack up my blanket and books, to get ready for my date.

* * *

 

**Jefferson**

It’s been two weeks and she hasn’t tried to text me, or call me. It’s so unusual. I’ve had to stop myself once or twice from reaching out to her. That is not part of the business arrangement I have, and I don’t want to jeopardize anything. I just can’t seem to get her out of my mind. 

Normally if I don’t contact the girl within the first two days, she’s blowing up my phone wanting to hang out again. I have to be careful though. If I’m hired to take her out on more than two dates, I have to end things the night of the third and then block her number. It’s alway hard when I see one of the girls around campus too; but somehow I manage. 

My phone rings and I recognize Chad’s number. “Hello?” 

“Hey, man. I’m in need of your services again for another date tonight with Y/N. Are you available?”

_ Shit. _ I am, but I was hoping it would be a one time service, I don’t want to get caught up in her more than I already am. I could lie and tell him I have another date; it’s not like he knows. I could always tell him the two of us didn’t get along and she never wants to see me again. 

“Hey, you still there?” He asks.

I rub my forehead. “Sorry, I was looking at my calendar.” I sigh. “Yeah, I’m free tonight.”

“Perfect. Aubrey told me Y/N’s been talking about you on and off since your last date. Guess that means things went well last time.”

_ There goes that thought of we didn’t get along. _ “Sure. I’ll get in touch with her and let you know when it’s set. This date falls into the same contract.”

“Sounds good. Best money I’m spending.” He sounds happy. “Thanks, man.” He hangs up the phone.

I wish I wasn’t doing this for the money. There’s something about Y/N. I want the chance to actually get to know her. Bring her on a real date. There’s no way that she would let me continue my business if we were to date for real.  _ What girl would allow that? _ I need this too, it really helps ease the burden of college expenses.   

I think about texting her; but that seems too impersonal, especially since we haven’t talked to one another since our last date.  _ If she’s been talking about me, why hasn’t she contacted me? _ She has my number as well, after all. I made sure we exchanged numbers before I dropped her off for the night, when she refused to let me walk her to her room. 

I stroll along campus, looking for her in her usual spots, and find her in the middle of the quad on a blanket with a book open. She looks content, sitting there, doing her own thing. She doesn’t even seem to notice the game of catch happening around her. I walk up to her.

“Always with your nose in a book.”

She looks up at me and squints; but I see the small smile playing on her lips. “Need to keep my grades up. What are you doing here?”

“Hoping to run into you. Mind if I sit down?”  _ Please say yes. _

“Sure.” 

I sit down and she goes back to reviewing her book. I can’t help but smile. I wait patiently for her to give me her attention again.

“Is there something you want to say?”

“You look really nice today. I like seeing you like this, in your element.”

She laughs, and it’s like music. “Strange compliment, but I’ll take it. Thanks. You look good yourself.”

I feel heat rise to my cheeks. I never blush, and I feel like I’m in middle school all over again, sitting next to the pretty girl. I mumble thanks and quickly move on to a safe topic. My job.

“So listen, Y/N, I was hoping we could have that date going out to see the stars?”

Her eyes light up, and her smile transforms her entire face. “Yeah, I’d like that a lot. When are you thinking?”  

“I checked the weather and it’s supposed to be a clear night. We could head out there tonight if you’re up for it.”

She nods, but doesn’t say anything else.

“Great, I’ll come by to get you at eight tonight to get you. Is there anything I should bring?” 

“No, just yourself and maybe a sweatshirt. It can get chilly at night.”

“Okay. I’ll see you tonight.” I stand and leave her sitting there. I pull my phone from my pocket and text Chad. 

_ All set. She’s going out with me tonight. _

_ You are amazing. Not sure how you do it. She refuses to go out with anyone. Guess I’m lucky I found you. _

Now I really feel like an ass. I’m setting her up to get hurt, and that’s the last thing I want to do. I’m playing with fire here, and I know it. 

I make it back to my apartment and put together a small picnic, and gather a blanket up. Chad wants us to stay out for a while, and I want to make sure I can deliver. 

I make it to her dorm at 7:55 and she is outside waiting for me. She jumps in the car, and starts rattling off directions for me. I can’t help my smile, she is so excited, and it shows. I’m making her happy; and I love it. Then I start thinking about what I’m doing, and why we are even here in the first place and my smile fades.

_ She’s a job.  _ Do  _ not _ get feelings for this girl. I berate myself the entire ride there as she talks animatedly. I put the car in park and reach in the back for the basket and blanket. She stares at me and blinks her eyes a few times.

“Is there something wrong?”

“Why do you have a picnic basket and blanket?”

I smirk. I surprised her alright. “So we can have a proper date and watch the stars. One must have food to call it a date.”

She shakes her head, trying to rid the smile that’s formed. “You’re something else. You know that right?”

“I’ve been told that a time or two.”

* * *

 

**Y/N**

_God, it’s really not fair. This man is perfect._ He knows just what to say and what to do to make me want to jump his bones. I’ve never felt this way about anyone, and it’s scary. I want to go back to how things were— just my books and my studies. 

“So, where is the perfect spot to set up for the evening to watch these stars?”

“Um,” I look around us. “Right over there is fine.” I point to a spot of grass and he walks over, spreading the blanket out. I stay where I am, and just stare at him.  _ Curiouser and curiouser. _ I can’t get the rumors out of my head though, and my mood changes. “Jefferson?”

He looks over at me and waits for me to continue. “Why are we on this second date? You didn’t call me or contact me for two weeks. I haven’t run into you on campus and…” you trail off.

He waits and when I don’t continue he asks. “And what?”

I huff. “Well, I’ve heard a few rumors about you around campus, and then there was that girl at Granny’s.”

“What rumors?”

“That you never get serious with a girl. After a few dates you dump them, or never contact them again. If you’re not serious about trying something, then you might as well bring me home tonight. I have enough going on, and I don’t need to complicate things with dating.”

He nods. “That’s fair. What you’ve heard is true; I don’t get involved. I have my reasons, just as you have yours. I would really like to enjoy the evening with you though. I brought some snacks, and we have the stars to keep us entertained. Maybe you can tell me about some of the constellations.”

I make my way to the blanket and sit down. He opens the picnic basket and pulls up some fresh fruit, cheese, crackers and a bottle of wine.  _ He has thought of everything. _

“Hope you like wine.”

“Yeah, that’s great, thanks. This spread looks amazing, Jefferson. You really didn’t have to do all of this. Thank you though.”

“What are friends for?”

He pulls the cork from the bottle and pours some into my glass. Taking a small sip, I enjoy the fruity flavors on my tongue and I look up at the sky. In another 30 minutes or so, it will be dark enough to see the vast amount of stars. I hug my knees to my chest and take a deep breath. I’m so relaxed out here, it’s my favorite spot to be.

We talk, eat, and laugh, waiting for the stars to come out. When they are finally visible enough, I tell him the story of some of the ones I recognize.

I point to a set of stars. “That’s Cassiopeia. She was condemned to the sky by Poseidon and she spends half her life upside down on her throne.”

“What did she do to piss Poseidon off?”

“She used to say how she was the prettiest out of everyone, including the sea nymphs. That enraged Poseidon’s wife, and since he was the God of the sea, she made him do it.”

“So basically she got sent up there because another woman was mad over something she said?” He laughs and pops a grape in his mouth. “Typical.” 

It really does sound ridiculous when he says it outloud and I can’t help the smile. “Yeah, that’s about right.” 

I finish my glass of wine and he pours another one for me. I have a small buzz going on and I gladly drink more, enjoying the warm, fuzzy feeling. I see him scoot a little closer from the corner of my eye, and his hand brushes over mine. I look up into his eyes and move a fraction of an inch closer. He leans closer and just before he touches my lips, he stops and hovers, making me close the distance if I so choose.

With my buzz and his warmth of his breath on my face, there’s nothing to decide. I want to kiss him just as bad. I close the gap and our lips touch. His are soft, plump, and warm against my own, and I can taste his wine from his mouth. I lean into him more and he wraps his hand around the side of my neck and cheek, deepening the kiss. 

He pulls away and a tiny needy moan escapes. I flutter my eyes open, looking into his lust blown blue ones. “What was that for?”

“You’re really pretty. I’ve wondered what your lips would feel like on mine for some time now. Gotta say, I’m not disappointed.” He smirks. 

I touch my lips with my fingers, my heart beating a mile a minute. “You’re welcome to do it again anytime.” I learn forward to kiss him again and my phone starts ringing, breaking the spell. “Sorry, hang on.” I look at the ID and it’s Aubrey. She never calls from her dates, and it’s too early for it to be over. I’m worried she’s in trouble so I answer. “Are you okay?”

“Y/N, are you with Jefferson?”

“Yeah, we’re stargazing. Why?”

“Chad paid him to go on a date with you.” 

I whip my head to look at him and he looks at me confused. “What do you mean? How do you know that?”

“I overheard him talking about it. He has a business where he gets paid to take girls out on dates. He calls himself,  _ The Mad Hatter. _ I ripped Chad a new one. I’m so sorry hun, I really thought this was genuine.”

“Fine, listen, I gotta go. I’ll see you a bit later.” I hang up the phone and keep staring at him. I down the rest of my wine, because I need all the courage I can get.

“Is she alright?” He rubs the back of his hand against my arm.

“Oh yeah, she’s great. Me on the other hand, not so good.” I snatch my arm back from him. “So your reasons for not getting involved are monetary huh?” I stand up, needing to distance myself from him.

“Fuck,” he mutters.

“Let me ask you, do you get paid extra if I fall for you? Do you get a bonus for sleeping with me?” 

He stands and takes a step closer, I take one back. “It’s not what you think, give me a chance to explain.”

I hold my hands up and give him a look of disgust. “I don’t want to hear it. Just leave. I’ll get a ride home myself.”


	3. Chapter 3

**Summary for the Chapter:**

> Jefferson has been caught. Are you willing to forgive him?

**Jefferson**

_ Shit. _ No one has ever found out before. I’m screwed. “Please, Y/N. You have to let me explain myself. You owe me that much.”

“I  _ owe  _ you? I don’t owe you shit, Jefferson. I never lied to you. I never led you on. You told me the reason you didn’t date was your own, and I can respect that; but this,” she extends her arms towards me and then crosses them over her chest, “this is so much much worse than anything. You’ve made me feel like a piece of meat.”

I hang my head. She’s right, and I know it. I need to tell her anyway, even if she won’t listen to me.

“Do you know you’re the first girl I wanted to date for real? Not for money, not because I have a contract; but because I genuinely thought you and I would have fun together. My business started as a joke, but the past few years it has been a way of making ends meet for college expenses.”

Her back is towards me, and I see her move her hand towards her face. I know she’s crying, and I hate the fact I’m the one that put the tears there.

“Jefferson, please just go. I’m going to call Aubrey and have her come get me.” 

“I’m not leaving you alone in the middle of the damn woods. If you don’t want to talk to me, fine. We won’t talk. I’m not leaving you though.”

She doesn’t turn around, just pulls out her phone and sends a text. I do the same; but mine is to Chad.

_ Jefferson: What the fuck are you thinking? _

_ Chad: Dude, I didn’t mean for it to come out, it just did.  _

_ Jefferson: You realize I no longer have a business because of you right? Word is going to spread about this so fast now. _

_ Chad: Seriously, I had no idea she was there. I was talking to some buddies and she was behind me. If it makes you feel better, Aubrey basically kicked my ass. _

_ Jefferson: It doesn’t. _

“Aubrey will be here in 15 minutes. No need to hang around.” She says, matter-of-factly.

“I already told you, I’m not leaving you here alone.” I look up at the sky and see a shooting star. “Hey look, a shooting star.” I point in the direction is comes from and she lifts her head to the sky. Here goes nothing _. I wish she never found out about my business and I wish I could start over with her again.  _ I look over at her, “What did you wish for?”

“I wish you would leave me alone.”

“Ah. You broke the first rule of wish making. You said it outloud, therefore it can’t come true, you’re stuck with me.” I smirk trying to show her I’m messing with her; and she almost snarls at me.

“Just answer me this one thing, because,” she pauses and scoffs, “I just really need to know.” I stay silent allowing her to ask. “The kiss. Did it mean anything, or was it part of the deal you had with Chad?”

I knew she was going to ask that. I want to tell her that I’ve wanted to do that since our last date. I don’t deserve her though, so I stay silent. 

“Wow. Hope Chad paid you a lot then. You turned out to be a bigger asshole than any other man I’ve met.”

* * *

 

**Y/N**

I walk towards the street, trying to hide the fit of tears that are trying to escape. I don’t want to see him ever again. I just want to go home, hop in the shower and then curl up in my bed, pretending this night never happened. The further I can get from him, the better. 

I know my way around these woods like the back of my hand, so I walk down the path that leads to the main road. If I can get away from him and his beautiful blue eyes, I might just be able to hold it together until Aubrey got there. I look down at my watch. It’s only been five minutes since I’ve called her. I feel like the biggest fool, for liking him in the first place. I was nothing to him but a pawn. 

I march back over to him, my anger in full effect now. He looks at me with hope in his eyes. “How do people get in touch with you? How does it all work?”

“Information is spread through word of mouth. Guys who are looking for me, post an ad on the school website asking for a call about a date. I’m the one that initiates contact and then meet with the...client.”

“How much are you charging for your services?” 

“I charge one hundred bucks per date.”

My eyes bug out of my head. “Wow, you must be loaded then. I’m sure you go on a ton of dates.”

He rubs the back of his neck, and chuckles. “Not really. I’ve hit a bit of a dry spell as of late. You are the only date I’ve been on in a few months.”

I can’t help myself, “Wow. You must have been desperate then to go out with me.”

“Y/N. Stop. This isn’t how I wanted you to find out about this. I wanted to take you on a real date, and tell you about it. You’re...different.” He closes the distance between us and I stand my ground. I was here first, after all. “I like you. I’ve liked you since our first date; but since I was hired for a job, I had to keep my distance.” He takes another step closer, and I can feel the warmth radiating off his body. “I’m sorry about how you found out, but I wanted to keep talking to you after all this was over, you have to believe me.”

“I don’t have to believe anything, Jefferson,” I whisper. I see car lights approach us and I take a step back. “Lose my number. I don’t want to talk to you.” 

I walk towards Aubrey car and jump into the passenger seat, closing it tight behind me.

“I can’t believe this. I am so sorry, Y/N. I seriously didn’t think Chad would ever stoop so low. I thought Jefferson was someone from a class, or an acquaintance or something.” 

Aubrey rambles when she’s upset, and I just let her do it. I look out the window and watch the trees fly past. My mind replays the night. It started off so perfect, and that kiss was something else. I touch my lips with my finger.

“You didn’t,” Aubrey interjects.

I drop my fingers and look at her. “Huh?”

“You kissed him, didn’t you?”

The tears start forming again. I can’t push the words past the lump in my throat and I nod. I  _ am _ the one that kissed him too. He gave me the option to back out; but I wanted it so bad.

“Oh babe. I’m so sorry, he’s low life scum. Any boy that does that should have his balls ripped off and be force fed them.”

I smirk, she always comes up with the best stuff when she’s angry.

* * *

 

**Jefferson**

I pack up everything and drive back to my apartment. I’m toast. She’s going to find a way of telling everyone what I did. I’m looking at disciplinary actions from the university, or worse—being blacklisted.  _ I’ll never get a date in this damn town again _ ! I need to find a way to fix this with her. This was the last thing I wanted.

I need to find a way to reach out to Y/N and make sure she knows just how sorry I am.  _ Flowers?  _ No, that will probably just piss her off. It’s the go to for every man when they’ve done something wrong.  _ A public apology? _ Then I’d have to do that for every girl who I ever dated—and that’s a lot. Although, I probably should if I don’t want to be castrated. I just need her to talk to me, to give me five minutes to explain everything better than I did tonight.

Then, the idea hits me. I’m going to make a public announcement in the quad, coming clean. I’m going to have a friend record it, and post it on the University website. I want every girl I’ve ever gone on a paid date with you know just how sorry I am. If I come clean, maybe Y/N will talk to me again.

I start hashing out the plan, and I text her, hoping she will come.

Me: Tomorrow at 11, meet me on the quad in your favorite spot.

Y/N: Stop bothering me.

Me: Please, after this I promise if you don’t want to see me, I’ll leave you alone. 

I wait...and wait….and wait; but I don’t get a response. I’m hoping that’s a yes; but I won’t know until tomorrow.

Word spread fast about my public announcement and there was a much larger crowd than I expected. I look through the familiar faces of the girls I’ve gone on dates with, and some of the guys that have paid me to do so. The one face I want to see in the crowd though, isn’t there. My face falls but I climb on the large rock and begin.

“Hi. I’m Jefferson Hatter. I’ve been on a date with several of you, and have been paid by several others. I want to publicly apologize for anyone that I’ve hurt through my actions. My intent was never to make you feel like a lesser person, or to deceive you, it was strictly business. I know this isn’t going to be enough to make it right with all of you; but I hope it’s a step in the right direction.”

“Since starting here at Storybrook University, I’ve worn many hats and it’s been difficult at times to make ends meet. This idea came to me sophomore year, and I’ve just rolled with it. Many of you ladies were very nice, and I enjoyed our dates; but it was just business.” I scan the audience and my eyes lock with hers. She is watching me intently, and my heart beats faster. 

“There is one girl though, that I didn’t want to lie to. I could have just gone on a date with her without taking the money; but I was greedy at the time. I’ve learned my lesson. I’m no longer  _ The Mad Hatter _ . My business has been shut down permanently. Thank you for listening to me.” 

I climb down from the rock and most of the crowd disperses, except a few of my previous dates. I wait for the verbal lashing; but it doesn’t come. They just look at me with pity in their eyes, and one of the girls says, “I appreciate the apology; but you’re right. It doesn’t make it right. No one wants to know someone had to be paid to go on a date with them.”

I ball my hands in fists, keeping them down to my sides. “I know. I truly am sorry; but you should also be lashing out at the man that hired me.”

She nods, her lips in a tight line. “Yes, and you’re going to give me that information.”

“Send me an email and I’ll make sure to get you the information.”

She walks off with the small crowd and I lock eyes with Y/N. I walk up to her, and she won’t look me in the eyes.

“I know I will never be able to say I’m sorry enough, but I meant every word I said. I didn’t know it was you, until I arrived that night and then I felt horrible.”

“Why did you accept the money for the second date then?”

“I fell down a rabbit hole, and I couldn’t stop. It was nice knowing I had some extra cash in my pocket. I’ve been used to it the past couple of years. I shouldn’t have done it.” I pull money out of my pocket and try to hand it to her. “Here, this is what Chad paid me for the dates.”

She pushes it back to me. “No. Giving me the money is worse than you getting paid.”

I blush, not even thinking about it like that. “That’s not how I meant it. I was just trying to give it to you so I can say our dates were real. I’d like to see you again, and take you on a date that I haven’t been paid to do. Would you be willing to give me a second chance?” 

I lock eyes with her, pleading with her to say yes. She tilts her head to the side, examining me. Finally, she responds. “I still have a lot of constellations to show you. Maybe you can pick me up tonight?”

My face lights up and she smiles back at me. “I’ll pick you up at eight tonight.”

“Good. And Jefferson?”

“Yeah?”

“You have a lot of making up to do. I fully expect to get more than a kiss tonight.” She wiggles her eyebrows letting me know exactly what we will be doing tonight.


	4. Chapter 4

**Summary for the Chapter:**

> Things have been patched up nicely between Jefferson and you. Are you both ready to take it to the next level?

**Notes for the Chapter:**

> There is smut in this chapter. This originally wasn't part of the story, and it was added at a later time. Reader beware.

**Jefferson**

Date number ten and I’m still nervous as hell. Y/N and I have been seeing a lot of each other lately—walking around campus, eating lunch together, hanging out to watch movies. Most of them have been just hanging out. I’ve seen her a lot the past three months; but classes are winding for the summer months and I’m not going to see her during those month. She lives a lot further from Storybrooke than me.

We haven’t had sex yet—not for her lack of trying I might add. I just want it to be special and I don’t want to rush into anything. My reputation still haunts me around campus, and I don’t want her being exiled like I feel sometimes. It’s my own fault I’m in this boat though, so I don’t say anything about it. 

I pull up outside her dorm and get out, walking to her door to get her. I knock and hold the bouquet of white roses in front of me, waiting patiently for her to answer. When she does, I almost drop the bouquet. There is a goddess standing in front of me and my knees shake a little. She is standing there in a short red dress and thigh highs. As she moves back to let me in I can see the top of the stockings, and I lick my lips.

“You got me roses?” she asks, taking them from me. I’m having problems getting my brain and mouth to communicate. She looks at me and giggle. “Cat got your tongue, Jefferson?”

“Holy shit,” I mutter. “You look amazing. Maybe a little overdressed for dinner and a movie though?”

She pushes her bottom lip out in a pout. “You don’t like it?”

“It’s not that, doll.” I tuck a loose strand of hair behind her ear and cup her face in my large hands. “You’re going to drive me insane all night wearing that. It’s going to be impossible to keep my hands off of you.”

She grins like a cheshire cat, “Good, that’s what I was hoping for.” She turns out of my embrace and sits on the edge of her bed, putting on a pair of heels. “Now, are you sure I can’t change your mind about going out? Aubrey is gone for the evening and we have my dorm to ourselves.” She places her foot back down on the ground and leans back on her hands, looking up at me through her lashes.

“You know I don’t want to rush things. I don’t want you doing something you may regret in the morning. People still talk about me around campus, and I don’t want your reputation tarnished because of me.”

She sits up, giving me her full attention. “Jefferson, you don’t think people talk about me too? I’m the girl that’s dating The Mad Hatter. The girl that got him to change his ways and actually commit. They gossip about me, just as much as they do about you.”

“I didn’t know that. Are you sure?”

“Yes. I hear the whispers and Aubrey is very good at telling them to shut up.”

“Fine, let’s make a deal. Let’s go have a nice evening together, and if it feels right when the night is winding down, we can move to the next level. Deal?”

“Deal.”

* * *

 

**Y/N**

I’m as giddy as a school girl. Dinner was lovely and the movie was fine. We sat in the back and I convinced him to make out with me halfway through the movie. Now, we are almost back to my dorm and everything feels electric. I’m aware of the way his breathing has become more ragged and how my palms have become a little sweaty. He keeps grinding his teeth too.

“Jefferson. Are you alright?”

He nods, but keeps his eyes on the road. “Do you not want to do this...with me?”

He whips his head to look at me. “No, doll. It’s not that at all.” He turns his attention back to the road. “I just don’t want you to regret anything.”

His words a sweet, and I can’t help the smile that crosses my features. “Jefferson, I like you. I want this—you. I want you.”

He doesn’t say anything as he pulls into a parking spot. I get out and he takes my hand, leading me towards my dorm. We get to the top of the stairs and I pull my key out.

“Are you coming in?” I ask, unlocking the door.

His lips are on mine as he backs me through the door and closes the door behind him. He walks me towards the bed, our lips never parting. My calves hit the edge and I tumble down, Jefferson coming with me. His body weight is comforting on top of me and I spread my legs, allowing him to fit snug between them. 

One hand tangles in my hair, while the other glides down my arm, leaving goosebumps in its wake. 

“Are you sure?” he asks, panting as he breaks the kiss. “I’m not going to be able to stop once we start, I want you too damn much.”

“I’m sure.” I lift my hips to brush along the bulge in his pants and he moans quietly. 

He sits up taking his shirt off and I reach forward, helping him undo the button on his pants. My fingers trace his chiseled body—I can’t want to feel him. Sitting up on my knees, I pull my dress over my head so I’m in my bra, panties and thigh highs attached to a garter.

“Do you have any idea what these are doing to me?” he asks, dragging his fingers up from my knees to the apex of my thighs. “All night long I was picturing seeing you just like this. Let me tell you, it’s not a disappointment at all. You’re beautiful, Y/N.”

I feel the heat rising to my cheeks and I look down. “Not so bad yourself, Jefferson.” He tilts my face up to his again and peppers my neck and jaw with kisses. I grip on to his shoulders to support myself and lean into his kisses. He tugs my hair, opening my neck up to him more and I feel myself get wet—each kiss sends a jolt straight through me.

He eases me down so I am lying on the bed and he pulls my panties down my legs, helping me pull them off my feet. He takes my right leg and kisses all the way up and hovers his mouth over my bare pussy. He looks up at me from between my legs and I tilt my hips towards him, silently telling him to keep going. His tongue darts out, flat and wide licking me all the way up. Then he dives in eating me out like a man on a mission. 

His mouth is warm and wet over me. His mouth, tongue and teeth are working my sensitive clit over and over and he circles my entrance with his finger. When I buck my hips up, he presses me back down and holds me firmly to the bed. His index finger slips into me and I clench around him, wanting more.

“Oh god, more,” I pant.

He obliges and inserts another finger, pressing against my g-spot over and over. I feel the beginning stages of my orgasm approach and I tangle my fingers through his hair, holding him close, as I explode around his tongue. He continues to lick and suck at me until I swat his head.

“Jefferson, stop. Too much!” 

He sits up, a giant smile on his face as he pulls his pants down and off. I sit halfway up, holding myself up on my elbows so I can watch him move. He stands at the end of the bed completely naked and my mouth salivates at the view. He. Is. Perfect.

“Can I play with him for a little?” I ask, biting my lip and smiling.

“Not this round. It’s been a while and if you start sucking him, I’m going to go to fast. Condoms?”

“Top drawer on the left.”

He opens the drawer and cocks his eyebrow at me. “Glow in the dark? Is that really necessary?”

I laugh and plop back on the bed, covering my eyes. “Aubrey thought it would be funny and te colors are so bright.” My body shakes from laughing as I hear the foil rip. I open my eyes, watching as he rolls it up over his impressive length. He crawls between my legs again, pushing them open enough to fit his frame comfortably. He sits on his heels and pulls me towards him, so my ass is in his lap. Lining up, he presses in and I hiss at the small burn.

He stops moving. “Are you alright?”

I lock eyes with him and nod. “Yeah, you’re just bigger than I’m used to. I’m fine.” I try wrapping my legs around his waist to pull him closer; but he holds back. “Please Jefferson, I want you.” 

He slows down and enters me slowly until he’s all the way in. We both breath for a minute as I adjust to his size, and he rocks his hips slowly, back and forth.

“Faster, Jefferson,” I pant, reaching forward to pull him towards my lips. He leans forward and presses his lips to mine, coaxing it open with his tongue. He reaches his hand down between our bodies and plays with my engorged clit. Moaning into his mouth I buck my hips in time with his thrust and I’m so close.

“I can feel you, you’re so close. Come for me, Y/N.” He pounds harder and faster into me, his hand rubbing tighter circles.

I arch my back as my orgasm washes over me. He sticks his arm under my lower back, pulling me flush to him as he reaches his own orgasm, moaning as he releases.

We both fall down on the bed and I play with his beautiful chestnut hair, his breath tickling my neck.

“You’re amazing, Y/N. That was perfect.”

“See what you’ve been missing? If only you listened to me sooner, we could have been doing this a lot longer.”

“Good thing I learn from mistakes. I won’t make this one again. I’m going to clean us up and then be ready for round two. I’m not done with you tonight. Actually, we might have to skip a few classes so I can keep you trapped in my bed for a few days.” He plants a quick kiss on my lips and pulls out to clean up.

“You really are crazy, Jefferson.”


End file.
